5 Times 1 Time
by NE8675309
Summary: 5 Times Jeff Woke Up Beside Annie 1 Time She Woke Up Beside Him. Brief snapshots of significant moments in the Milady/Milord relationship after Annie returns home from DC. Post S6.


**A/N - Back again to bug you guys, lol. This story started to come together in a small, out of nowhere brainstorm session with my cousin. One of us mentioned a quickwrite kind of fanfiction and talked about Jeff waking up beside Annie the day after their wedding. I really liked the idea and decided to run with it, but quickly realized it was too short and vague to stand alone as a fanfic. I decided to go with one of those '5 Times + 1 Time' prompts and I skewed it slightly to better serve what I was trying to go for. I hope I was successful in creating what I had originally envisioned, if that makes any sense, lol. I think I might be open to try more '5 Times + 1 Time' prompts with them as the subject matter. Anyways... enjoy. Thank you.**

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 _ **5 Times Jeff Woke Up Beside Annie + 1 Time She Woke Up Beside Him  
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 **1.**

As memories of the night before flooded in with the morning light, Jeff Winger couldn't help but think he hadn't meant for it to happen. Although as he awoke to the sound of soft and calm breathing for the first time in years, he had to admit that even if he hadn't meant for it, he had wanted it. He picked her up as a friend. He took her out for a celebratory drink as a friend. And she kissed him, uncorking feelings that had been lidded for too long. It was her fault, but he couldn't blame her for possessing the courage he did not and beating him to the punch.

As Annie's peaceful breaths filled his room and held him captive, his mind reeled and ached in wonder. What had the kiss meant for her? What had last night meant to her? He knew what it meant for him, to him. He had wanted this for longer than he could admit to and he definitely felt the difference it had made on him. He hadn't ' _slept_ ' with a woman since Slater and even then it was something he forced himself to do, because he saw it as an obligation expected of him as being part of a couple, but last night he became so relaxed beside her and hearing her breath begin to steady filled him with peace.

In truth, he'd always felt bothered after sex, almost guilty and now he realized that the sex that preceded it hadn't even been worth the aftertaste, but last night… He had never felt that there could be another layer to it, feeling connected to someone, being in charge of fulfilling their needs and even beyond that, wanting to. If Annie wanted him to kiss her or touch her softly, he had to, needed to. It was as if they had been calling to one another for far too long for a single request to be denied. It sounded overly sentimental in his head, but made him realize that being in love with the person made all the difference; not that he could tell her that.

As he felt her body stretch and heard what resembled a squeak erupt from her, he stilled even his own thoughts and watched her. She quickly froze in response to his practiced steady breathing. An array of sighs and small huffs escaped her in the moments of silent reflection and Jeff felt his gut tighten. He had just got her back after the longest 3 months of his life and he knew that the overthinking he was doing was nothing compared to what Annie's mind was capable of. The fact that she hadn't turned back to confirm his presence brought him some comfort, at least she remembered everything.

Just when he thought he couldn't handle the suspense anymore, he felt her attempt to roll away (probably hoping to escape) when his body moved of its own volition. He couldn't believe or stop himself for pulling her closer. He had never been a cuddling guy, ever. Even though the movement was meant to practically trap her (a panic reflex, he guessed) he enjoyed how her body seemed to meld right into his. He no longer feared her disappearing on him. The panic started to subside after 15 seconds without her pulling away. It was replaced with relief when she took a deep breath and snuggled closer into his arms. Only then did his breathing return and he felt hopeful.

Although every kiss had been Annie's idea, he decided to take the initiative, as he pulled her even closer nuzzling her somehow still silky, but messy hair and leaning forward placed a kiss on her cheek, he felt her smile and decided to acknowledge that they were both awake. "So," at the sound of his gravelly voice, he felt her stir and her thick eyelashes flutter. "Should we maybe tal-"

She made a sound from deep in her throat. "Nope." She turned in his arms and moved him so he lay flat on his back. She cuddled up to his side and draped herself across his chest. "Five more minutes." She said with a grin.

Jeff let his arm lay against her bare back and let his fingers skim and tease back and forth tickling the sensitive skin. She smiled against his chest and he was so thankful that she kissed him the night before.

 **2.**

Jeff opened his eyes and felt his gut still tied in knots. Last night had been a minor disaster. He looked at Annie's hunched over back. She only had stayed over because he argued it was too late for her to go home, but she definitely had wanted to. It had started out as a small fight, a tiff at most, but Annie seemed hell-bent on looking for larger issues in the trivial argument.

She said her anger had little to do with Britta, and maybe he wasn't paying attention to her explanation, because he still didn't see what it was supposedly about. She confronted him about confiding in Britta. At first he accused her of being jealous, which made sense. Even if Britta and he were a disaster, they still had history. Annie laughed; it was a sound full of scorn. She claimed that it had nothing to do with jealousy; Britta was her friend and she knew her well enough to trust her; which made him wonder if she trusted him as much, because she didn't say so. She had said, "I don't mind you confiding in a friend; in fact, I encourage it, but if you have a problem, I need you to come to me. I want us to be a team and I can't fix what's bothering you, if you don't tell me."

Now that he thought about it, she did have a point. For the past few months everything had been going great with Annie, too great; he had officially become afraid of picking a fight with her, even though he often wanted to. They were usually small problems, tiny annoying habits, just little things that weren't worth jeopardizing what he had been wanting for so long and that was Annie. So he kept his mouth shut and then tended to overindulge his need to rant when he went to Britta's bar, but she had turned on him and tattled to Annie. "Why can't you be upfront with me?"

"Why does it matter?

"Because it does. What is the point of this if you're not going to be honest with me? Fighting is not new for us; I'd rather be pissed at you after we've cleared the air, than think that everything's okay, because my boyfriend refuses to communicate with me. Don't you think we can withstand a fight?"

"Of course."

"Then why are you so afraid to test it?"

"Because I love you and I don't want this to end." He blurted and she had not handled it well. She hadn't exchanged the sentiments he had divulged and she had definitely gone to bed angry, claiming that she wouldn't continue the conversation if he was just going to get hysterical and change the subject.

Jeff had never been called hysterical and being called that for the first time by Annie, of all people wounded his ego, especially since he was being genuine about something he had known for a while, but hadn't had the courage to say. She had almost acted as if he had said that he loved her in hopes of winning the fight. If anything, it almost insured that he wouldn't, because it gave her leverage, though he knew Annie wasn't so warped as to see it that way.

He did love her though, and he'd known it for almost two years. He had been so afraid to tell her that it had been bubbling just underneath the surface waiting to slip out at the most inopportune moment. It was a scary thing to admit; Jeff had never really been in love with anybody and he wasn't quite sure that Annie was as invested as he was. She had so much ahead of her and for all he knew their relationship could have just been her indulging 6 year old curiosity. Maybe this was a fling that had reached its expiration date and he didn't know how he would handle that or if he could.

He knew she was right though. Even though he meant what he had said and even though saying it was an accident, it had completely undermined a very really issue that she had wanted to work out. He would try not to grovel, but he did need to let her know that he understood what she was saying and what she meant. He leaned over and pulled her huddled sleeping form into his chest. He kissed her on the cheek and she sighed contentedly, which was a good sign.

She turned around and wrapped her leg over him and pressed her palm to his bare chest. Her eyes were fluttering, but not opening, as he spoke. "So does this mean you forgive me?"

She replied with her eyes still closed. "No, but I love you." She looked at him and smiled softly. "And I'm starting to think that is more important."

He couldn't help but breathe a sigh of relief and kissed her. He wanted to let the fight die, but he knew that he owed her more than that. He felt more willing to mention it now that he knew they were both in the same place. "You were right. I'm sorry."

Her eyes regarded him softly. "Let's talk about it later."

 **3.**

Jeff awoke with a stretch and smile as his dream faded away. Annie lay on her back, brows knitted together. She let out a huff followed by small sighs. When her head twitched, Jeff couldn't hide a small laugh.

Her eyebrows smoothed, but her eyes stayed closed. "Are you watching me?"

He smiled. "I'm just deciding if I should give you a Sharpie beard to match the mustache I already gave you."

She opened her eyes and looked completely unconcerned, pushing out her lips and then turning her face slightly to the side, modeling the mustache that obviously wasn't there. "Does it make me look distinguished?"

He grinned back and nodded his head. "I've always wanted a girlfriend that's handsome."

She looked uncharacteristically serious for a second. "At least one of us should be." She smirked.

"Smart." He appraised snidely.

"Again, at least one of us should be." She poked a dimple in his cheek.

"Maybe moving in together wasn't such a good idea. I mean, I'm not handsome or smart-"

"Or funny." She grinned and interrupted encouragingly.

"Right, or funny. Thank you for that." She nodded and he continued. "So you see, this is doomed, because according to you I have nothing going for me. I can't begin to understand why you are even still here."

"Oh, that's easy." She smiled softly and began to lean in. Before their lips touched, she whispered. "I'm a firm believer in charitable giving."

He moved back, playfully offended. "You little shit!"

She grinned at the endearment, so he pinched her. She immediately held her hands up. "I surrender."

He stopped and looked at her flushed cheeks. "Maybe I don't accept your surrender."

"Do you think you could be persuaded to?" She said seductively. "You haven't heard my terms."

"Possibly." He answered.

She leaned in and kissed him softly. "We can christen the new place."

"I think I've been persuaded." He pulled her into his arms and kissed her. She rolled onto his chest and groaned loudly. "What?" He asked, concerned.

"What did you do to me last night?" She gave up trying to sit up and laid her chin on his chest.

"Nothing." He laughed. "You did that to yourself."

"How?" She inquired, baffled.

"How do you think? Who was the one that thought it would be fun if we finished all the moving last night without taking a break? I swear, by how you moved, I'm starting to think performance-enhancing drugs were involved."

She groaned again. "I'm so sore."

"And not for any of the fun reasons." He tsked.

"Hey, getting our home together was plenty of fun for me." She defended.

"I don't doubt that, but was the urgency necessary?"

She huffed. "Not totally."

He pushed a hair out of her face and tucked it behind her ear. "It's going to be nice, to always wake up next to you." His thumb smoothed along her cheek and she leaned into the touch.

She smiled. "'Always' is a strong word."

"I know what I meant." He leaned in and kissed her gently.

 **4.**

Jeff awoke to the sound of soft rain tickling the window. It had been raining since yesterday afternoon. The rain first started to come down when they stood outside facing one another and Annie's dress was quickly soaked. She surprised everyone by laughing; her face contorted in joy and they kissed.

Jeff had felt guilty during the reception as if he could've somehow controlled the weather. She told him it was fine, but he didn't believe her until she pulled him out for their 2nd dance as husband and wife. She kept walking until they were no longer under cover from the sprinkling mist. She swayed in his arms, letting the rain fall on them and he realized she wasn't just being a good sport.

He pulled away slightly and looked at her. "What?" She asked defensively with a smile. "I've never danced in the rain before."

He touched her face gently and tried to look behind her smile. "How are you handling all of this so well?" She placed her hand on top of his, but he continued. "Today has kind of been a disaster. The flowers never arrived, several non-RSVP's came and with dates, they sent out the wrong cake and you're nearly soaked through because it started raining in the middle of our vows."

She smirked good-naturedly and addressed each issue. "The only flowers that matter were the bouquets and those are all here. The more the merrier. I personally kind of like the 2 groom figures and a little rain never hurt anyone. I actually am enjoying it; it makes today even more memorable."

"But-" Jeff hadn't been trying to complain. To him a wedding was just a big party; and it wasn't as if he wanted her to whine, but he didn't want her to pretend to be happy if she was upset. He couldn't even mention her lack of familial guests.

Abed had given her away; she said if Pierce had still been alive, she would've asked him. However, she insisted that Abed was the most qualified seeing how close they had grown when they were roommates. "You've been planning your wedding for years. You already had to compromise so much." They had split the cost almost evenly, minus a little help from his mother and Jeff could only afford so much on a Greendale teacher's salary. He wanted to be able to give her everything she wanted, she had definitely earned it all. Not even an hour into their marriage and he felt like he had already failed her. "Nothing went as planned."

"And?" She beamed. "I'm happy for that. If everything had always gone as planned, I would've never gone to Greendale, we would've never met. Sometimes you have to eschew plans for something better. Today almost seems fitting for us; nothing in our relationship, even from the beginning, has went as planned, but I have loved every second of it, of you, and I am thankful." Annie then pulled his hand from her cheek and kissed his wet palm. "And you're wrong. One thing went as planned today, the only thing that mattered. I married you. That's it. That's all I needed. That's all I wanted." In that second he couldn't help but be overwhelmed by how lucky he was.

He looked over at her now and smiled. Her nose was a little red and puffy from all the dancing in the rain; her hair was naturally curled after air-drying into a beautiful mess that seemed to wholly personify his sleeping wife. His 'wife'? The thought settled in his mind for a second. They had been planning the wedding for months, he knew this had been coming; he had even imagined what it would be like to be married to Annie (more than he might admit) so this had been the end goal, but it still was baffling to wake up and be a husband, Annie's husband.

Jeff's finger felt heavy, weighed down by the gold band. Not a shackle, but a tether, a reminder that he now had someone relying on him; not necessarily to provide or protect, but to be dependable, present and honest. He and Annie were a team, he'd always known that, but now they had made a vow on that bond. He couldn't afford to be selfish and apathetic, where Annie and his promise were concerned. It was humbling and terrifying; exciting and overwhelming; amazing and shocking, but there was no one else in the world he would choose to do it for, or with.

He pulled her hair out of her face and played with it for a second. "Babe." No response. "Annie." Again, nothing.

He smirked. "Good morning, Mrs. Winger."

She stretched with a smile, a high yip and half opened eyes. Then she made a deep throat hum and laid the top half of her body across his chest, just as she often did. Her soft hair tickled his skin. He played with her hair for a minute. "Annie, it's time to get up. Our flight leaves in almost 3 hours. We have to get ready."

"No." She nonchalantly said, the sound reverberating from the back of her throat, almost like a purr. "Five more minutes."

They might end up running late for their own Honeymoon, but who was he to say 'No,' to Mrs. Winger today?

 **5.**

Jeff smiled as he opened his eyes and wrapped his arms around his wife's large and ever-growing belly. He kissed her cheek and felt her stir. "Happy Mother's Day." He murmured into her ear. He received a huff that he quickly interpreted to be a laugh, in response.

Before he could finish rolling back around towards the door, he was kneed in the groin by an overly enthusiastic three year old. "Daddy, Daddy, Dad-"

"Yes, Zooey?" He gestured for her to speak quietly.

She 'whispered' in the way that only a three year old could. "Are we making b-"

"Shh, yes. Come on, Z." He quickly threw on a T-shirt and lifted his daughter into his arms as he hurried into the kitchen.

He pulled her thick brown curls into a ponytail and placed a stepstool in front of the sink so they could both wash their hands. He gave her small tasks so she could feel like she contributed, all the while, following her with a towel to clean up her little messes.

After 'they' finished crafting a plate for Annie, Jeff set aside leftovers for them. Zooey tried to grab the tray off the counter and Jeff felt a small panic attack at the sight. "Whoa!" He grabbed the tray. "Z, this is too heavy for you. I have to bring it in."

"But, Daddy, I wanted to bring Mommy the food…" She pouted as her eyes got glossy.

If there was one thing Jeffrey Winger had a hard time saying 'No,' to, it was a request from the certain owner of blue Disney doe eyes; however, it was a whole other ball game refusing his angelic daughter with those same eyes, an even deeper shade of blue (glossy to boot), with her round cheeks and dimples. Jeff did not possess the restraint to reject anything she wanted. He was only human.

He set the tray down on the countertop beside him and kneeled in front of her. "Zooey, the tray is too heavy. You could hurt yourself or Mommy." She looked so hopeless and dejected as he pushed a stray curl out of her face. "But, I have an even more important job for you." She perked up noticeably. "I need you to grab Mommy's card and those flowers you picked out for her and bring them." She grinned and ran to retrieve the items.

A minute later they both went into the master bedroom. He set the tray down on her nightstand and noticed his wife was uncommonly still. He felt a quick and strong panic seize and thud throughout his gut. It ended as soon as Annie's eyes popped open, grabbing their daughter in a fit of giggles, leaving Jeff feeling ridiculous and almost strained, but relieved. "Happy Mother's Day!" Zooey gave her mother the card and flowers.

"Oh, so pretty." Annie sat up and sniffed the flowers. "I love them. Thank you." She read the card and pulled Zooey in for another hug. Jeff helped her up onto the bed. He leaned over and gave Annie a quick kiss. She beamed.

"Look, Mommy. We made you breakfast."

"Oh, man that looks so yummy." She took a bite of bacon. "Mm, so delicious. Be honest, Zooey, did Daddy help at all? This is too good to be his cooking."

"Well," The toddler considered. "He helped a little bit."

The two loves of his life began laughing when Jeff's mouth went agape with a gasp, Annie even more so. "Abed would die if he saw you with that expression." She leaned in and kissed him.

"Mommy, what about Sebastian? Did he get you a present?" She touched her mother's belly.

"Sure, he rolled onto my bladder several times, keeping me up all night." Jeff smiled and chuckled. "If we can consider that a present."

"Don't worry, Mommy." Zooey hugged her belly. "I'll teach him how to make bacon."

Annie smiled and played with her daughter's hair. Jeff interjected. "You mean, I'll teach you both."

He came around the bed and sat on his side. Annie turned to face him as their daughter began picking off her plate. "Thank you." She placed her palm on his cheek and as she kissed him, he could feel the cool gold band caressing his skin and her finger. "I love you."

Jeff couldn't stop his reflex to grin. "I love you, too." He put his arm around her and kissed her forehead. He looked at his daughter and pregnant wife and couldn't help but think that 10 years ago the vision would have filled him with dread, when the true reality was; he couldn't be happier or more fulfilled. "Thank you."

"For what?" Her brow lifted with a shy smile.

"I'll tell you later." He was so thankful for many things; that she joined the Study Group, that she cared enough to help him grow as a person, but most importantly, he was thankful that she had kissed him that night five years before when she came home; he couldn't imagine what his life would be if she hadn't.

 **+1 Time**

Annie awoke with a small stretch of her spine as an overpowering relief tethered throughout her chest. As she let an unburdened breath escape her she stilled as she heard its echo behind her. She felt a strong warm beating chest pressed against her back and contentment had been acknowledged, as the natural disoriented feeling each morning brought faded away and she realized that she was lying in a strange bed beside a one naked Jeff Winger. Once she remembered where she was and who she was with, a strong sensation of (well, she didn't want to say panic) but something closely resembling it threatened her peace of mind and began to turn relief into dread. 'What now?' She thought as the events of the night before bombarded her. It wasn't supposed to happen. Jeff had picked her up from the airport with no persuasion, in fact, he had offered, saying he would take her out for a drink, which meant her luggage was still in his car. She had to silence a groan at the reminder.

He had taken her somewhere new, claiming that Britta's bar, The Vatican, which they had frequented usually wasn't grand enough to celebrate her accomplishment of interning with the FBI. He was attentive throughout the night, asking her all about it, listening intently, smiling fondly, all the while wearing the same soft eyes that knew how to tear her to shreds. She never meant for anything to happen, but being with him again and remembering how he kissed her goodbye and looked at her, the same way he was at that moment. She had to kiss him, there was no other option. When he kissed her back, it was like being transported back to Greendale and standing in front of the library 5 years before, with something more lingering in the kiss. There wasn't much discussion after that, considering that they couldn't keep their hands off each other and their mouths were otherwise occupied.

She lay beside him and had no idea what any of it meant. When he had said goodbye 3 months before, was that something more or was he saying goodbye to a conquest. Is that what she was, is that what this was?

Annie was ashamed to admit that she was naïve when it came to men, none more so than Jeffrey Winger. Was this like his situation with Britta? Was she supposed to leave now? Because she would, if she could; better to be safe than sorry, however, all her possessions were still in the trunk of his car, including her purse and keys. She could call Britta, but then she would have to explain where she was and why, which would lead to a whole other line of questioning that she definitely wasn't ready for and didn't know the answers to (well, some of them she would know the answers to). She could feel herself blush. Plus, if this was a mistake, she shouldn't let news of it spread.

It hadn't felt like a mistake. It had left her… discombobulated; it wasn't bad, on the contrary, if she had to describe it, it felt right. Despite the small fear and anxiety, it had felt natural; new and familiar all at the same time. It hurt a little to think that after such an amazing night, that the first thought going through her head was a need to escape. Jeff was skittish and definitely had a track record; if this night had meant anything to anyone, it was Annie. All things considered though, she was happy she started it by kissing him, even if it complicated things, or possibly wrecked them; it almost felt worth it.

Her panic began to refuel and she felt restless as if she should just walk out of his apartment possession-less. She tried to think of the upsides to becoming a monk-like hermit when her attempt to roll off the bed was thwarted by two strong arms surrounding her in a barricade that enveloped her in his breath, his smell and his warmth, pulling her close to him. Although a million questions filled her head, she was happy to have one answered, he wanted her there. And as the sunlight poured in through the room, with his arms wrapped protectively and affectionately around her as their breathing synced up, she knew she wanted to be there too. Even if everything became a mess later, something deep in her gut told her it was important that she stay there today in his arms.

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 **A/N PT 2 - BTW, I might be the only one who thinks so obsessively about Community, but I would like to let it be amended that Annie is eating some kind of bacon substitute. Just want to keep myself safe from people coming at me with 'That's not Kosher' etc. Okay, I know, I'm overthinking it... Dork. :)**

 **Also, I am currently working on 2 (or 4, not quite sure yet) other Milady/Milord fanfics. One is supposed to be a quickwrite, so I hope I'm finished with that soon; the other will probably take quite a bit longer, unless I get carried away, like I did with _Resolved_. Not sure if anyone's curious, just thought I would give an update.**


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